Methyl iodide → 4-Chloro-5-methyl-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

HRID 28922ノート

反応式

HRID 28922 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Li][CH:22](CC)C.CI>O1CCCC1>[Cl:1][C:2]1[C:7]([CH3:22])=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=12

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

生成物 1

HCID 242292764-Chloro-5-methyl-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold −78° C. solution of 4-chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine (3.24 mmol, prepared as described in Tetrahedron Lett. 2004, 45, 2317-2319), in dry tetrahydrofuran (22 mL) was added 1.4M sec-BuLi in hexanes (7.12 mmol) dropwise over 5 min. After 30 min, methyliodide (10.5 mmol) was added. After 45 min, the reaction mixture was quenched with saturated aqueous ammonium chloride (25 mL) and diluted with ethyl acetate (25 mL). The extracts were dried over sodium sulfate, filtered, concentrated under reduced pressure and the residue was purified by silica gel chromatography (100% hexanes) to give the title product as a white solid (86%). ESMS [M+H]+: 323.2

後処理

  1. waitAfter 45 min
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (25 mL)
  3. additiondiluted with ethyl acetate (25 mL)
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (100% hexanes)

出典と根拠

ORDレコード
ord-35fa8b8c0f8e4c1c9628340e1108a25a
出典データセット
uspto-grants-2008_09
特許番号
US07419988B2

反応ノート

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